2-Methyl-3-hydroxy-4-acetyl-5-vinylpyridine → 2-Methyl-3-hydroxy-4-(2-hydroxybut-2-yl)-5-vinylpyridine

Participants

Reaction Steps

A solution of 3.93 g. of the product from Step A in 200 ml. of tetrahydrofuran was treated dropwise with 110% excess of ethyl magnesium bromide in tetrahydrofuran. After aging 2 days at ambient temperature the reaction was quenched on ice-water (100 ml.) containing 10 g. of ammonium chloride. The aqueous layer was separated and extracted with ether. The combined organic layers were dried over magnesium sulfate and evaporated to dryness to give 2-methyl-3-hydroxy-4-(2-hydroxybut-2-yl)-5-vinylpyridine, which was used directly in the next step.

Provenance & Evidence